RU2014153679A

RU2014153679A - HETEROCYCLIC ANTI-MICROBIAL COMPOUNDS FOR USE IN WATER-CONTAINING SYSTEMS

Info

Publication number: RU2014153679A
Application number: RU2014153679A
Authority: RU
Inventors: Чарлз Э. КОБЁРН; Асгхар А. ПИРА; Хитер Р. МАКДЖИНЛИ; Томас КЁЛЕР
Original assignee: Дау Глоубл Текнолоджиз Ллк; Ром Энд Хаас Компани
Priority date: 2012-06-19
Filing date: 2013-06-12
Publication date: 2016-08-10
Also published as: CN104603135B; BR112014030571B1; BR112014030571A2; RU2656592C2; AU2013277511A1; AU2013277511B2; PL2861592T3; JP2015523358A; JP6250656B2; US20150336983A1; CA2876015C; US9617278B2; AR091452A1; CN104603135A; CA2876015A1; IN2014DN10069A; EP2861592A1; EP2861592B1; WO2013191988A1

Abstract

1. Соединение формулы Iв которой n равно 0 или 1; R, Rи Rнезависимо обозначают Н, линейный или разветвленный С-С-алкил или С-С-циклоалкил или Rи Rвместе с атомом углерода, к которому они присоединены, образуют С-С-циклоалкил; и X обозначает О или NR, где Rобозначает Н или C-C-алкил, при условии, что соединением не является 2,3,4,8,9,9а-гексагидропиридо[2,1-b][1,3]оксазин.2. Соединение по п. 1, в котором Rобозначает Н и Rи Rнезависимо обозначают линейный или разветвленный C-С-алкил.3. Соединение по п. 1, в котором Rобозначает Н и Rи Rнезависимо обозначают линейный или разветвленный C-С-алкил.4. Соединение по любому из п.п. 1-3, в котором n равно 0.5. Соединение по п. 1, в котором X обозначает О.6. Соединение по п. 1, которым является: 2-бутил-3-этил-3,7,8,8а-тетрагидро-2Н-оксазоло[3,2-а]пиридин; 2′,7′,8′,8а′-тетрагидроспиро[циклогексан-1,3′-оксазоло[3,2-а]пиридин]; 2-(гептан-3-ил)-3-метил-3,7,8,8а-тетрагидро-2Н-оксазоло[3,2-а]пиридин; 2,3-диметил-3,7,8,8а-тетрагидро-2Н-оксазоло[3,2-а]пиридин; 3,3-диметил-3,7,8,8а-тетрагидро-2Н-оксазоло[3,2-а]пиридин или 2-этил-2,3,4,8,9,9а-гексагидро-1Н-пиридо[1,2-а]пиримидин.7. Способ борьбы с микроорганизмами в водных или содержащих воду системах или в системах, которые подвергаются воздействию влаги, способ включает взаимодействие системы с соединением формулы Iв которой n равно 0 или 1; R, Rи Rнезависимо обозначают Н, линейный или разветвленный C-С-алкил или С-С-циклоалкил, или Rи Rвместе с атомом углерода, к которому они присоединены, образуют С-С-циклоалкил; и X обозначает О или NR, где Rобозначает Н или С-С-алкил.8. Способ по п. 7, в котором Rобозначает Н и Rи Rнезависимо обозначают линейный или разветвленный С-С-алкил.9. Способ по п. 7, в котором Rобозначает Н и Rи Rнезависимо обозначают линейный или разветвленный C-С-алкил.10. Способ по любому из п.п. 7-9, в котором n равно 0.11. Способ по п. 7, в котором X обозначает О.12. Способ по п. 7, в1. The compound of formula I in which n is 0 or 1; R, R and R are independently H, linear or branched C — C alkyl or C — C cycloalkyl, or R and R, together with the carbon atom to which they are attached, form C — C-cycloalkyl; and X is O or NR, where R is H or CC-alkyl, provided that the compound is not 2,3,4,8,9,9a-hexahydropyrido [2,1-b] [1,3] oxazine. 2 . A compound according to claim 1, in which R is H and R and R are independently linear or branched C-C alkyl. A compound according to claim 1, in which R is H and R and R are independently linear or branched C-C alkyl. The compound according to any one of paragraphs. 1-3, in which n is 0.5. The compound of claim 1, wherein X is O.6. The compound of claim 1, which is: 2-butyl-3-ethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2 ′, 7 ′, 8 ′, 8a′-tetrahydrospiro [cyclohexane-1,3′-oxazolo [3,2-a] pyridine]; 2- (heptan-3-yl) -3-methyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 3,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine or 2-ethyl-2,3,4,8,9,9a-hexahydro-1H-pyrido [ 1,2-a] pyrimidine. 7. A method of controlling microorganisms in aqueous or water-containing systems or in systems that are exposed to moisture, the method includes reacting a system with a compound of formula I wherein n is 0 or 1; R, R and R are independently H, linear or branched C — C alkyl or C — C cycloalkyl, or R and R, together with the carbon atom to which they are attached, form C — C cycloalkyl; and X is O or NR, where R is H or C-Calkyl. 8. The method according to claim 7, wherein R is H and R and R are independently linear or branched C — C alkyl. The method according to claim 7, wherein R is H and R and R are independently linear or branched C-C alkyl. The method according to any one of paragraphs. 7-9, in which n is 0.11. The method of claim 7, wherein X is O.12. The method of claim 7, c

Claims

1. The compound of formula I

in which n is 0 or 1; R ¹ , R ² and R ³ independently represent H, a linear or branched C ₁ -C ₁₀ -alkyl or C ₃ -C ₈ -cycloalkyl or R ² and R ³ together with the carbon atom to which they are attached form C ₃ - C ₈ cycloalkyl; and X is O or NR ⁴ , where R ⁴ is H or C ₁ -C ₆ alkyl, provided that the compound is not 2,3,4,8,9,9a-hexahydropyrido [2,1-b] [ 1,3] oxazine.

2. The compound of claim 1, wherein R ¹ is H and R ² and R ^{3 are} independently linear or branched C ₁ -C ₁₀ alkyl.

3. The compound of claim 1, wherein R ³ is H and R ¹ and R ^{2 are} independently linear or branched C ₁ -C ₁₀ alkyl.

4. The compound according to any one of paragraphs. 1-3, in which n is 0.

5. The compound of claim 1, wherein X is O.

6. The compound according to claim 1, which is: 2-butyl-3-ethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2 ′, 7 ′, 8 ′, 8a′-tetrahydrospiro [cyclohexane-1,3′-oxazolo [3,2-a] pyridine]; 2- (heptan-3-yl) -3-methyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 3,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine or 2-ethyl-2,3,4,8,9,9a-hexahydro-1H-pyrido [ 1,2-a] pyrimidine.

7. A method of controlling microorganisms in aqueous or water-containing systems or in systems that are exposed to moisture, the method includes reacting the system with a compound of formula I

in which n is 0 or 1; R ¹ , R ² and R ³ independently represent H, a linear or branched C ₁ -C ₁₀ -alkyl or C ₃ -C ₈ -cycloalkyl, or R ² and R ³ together with the carbon atom to which they are attached form C ₃ -C ₈ cycloalkyl; and X is O or NR ⁴ , where R ⁴ is H or C ₁ -C ₆ alkyl.

8. The method of claim 7, wherein R ¹ is H and R ² and R ^{3 are} independently linear or branched C ₁ -C ₁₀ alkyl.

9. The method of claim 7, wherein R ³ is H and R ¹ and R ^{2 are} independently linear or branched C ₁ -C ₁₀ alkyl.

10. The method according to any one of paragraphs. 7-9, in which n is 0.

11. The method of claim 7, wherein X is O.

12. The method of claim 7, wherein the compound is: 2-butyl-3-ethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2 ′, 7 ′, 8 ′, 8a′-tetrahydrospiro [cyclohexane-1,3′-oxazolo [3,2-a] pyridine]; 2- (heptan-3-yl) -3-methyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 3,3-dimethyl-3,7,8,8a-tetrahydro-2H-oxazolo [3,2-a] pyridine; 2,3,4,8,9,9a-hexahydro-pyrido [2,1-b] [1,3] oxazine or 2-ethyl-2,3,4,8,9,9a-hexahydro-1H-pyrido [1 , 2-a] pyrimidine.

13. The method of claim 7, wherein the system is at a temperature of at least 40 ° C.

14. The method according to claim 7, in which the system is a liquid for oil or gas production, recycled water of a paper machine, industrial recycle water, starch solution, emulsion of latex or polymer, a product for coating or construction, or a household product, or means for personal hygiene products that are produced at elevated temperatures, plastic products, cutting fluids, industrial liquid for washing dishes or washing, liquid for protecting animals from biological effects tviya or highly active liquid for disinfection.

15. The method according to claim 7, in which the system is a fracturing fluid, drilling fluid, water for flooding, produced water or produced fluid.